Dating A Woman For The First Time

Dating A Woman For The First Time

Dating a woman for the first time felt like a scary adventure. But one that taught me so much.

I knew I was bisexual from a young age, and had played with women here and there.

But, my relationships had been predominately with men. Women were always these gorgeous creatures, almost mythical. I was too scared to flirt with women, always worried I’d mess up and they would give me a “you are talking to me?!” look, but maybe that’s just my anxiety speaking.

Then I met J, and we fell into a love affair that was like fireworks, burning bright and fast. J made my heart pitter-patter. We met through mutual friends at a party, we became friendly and then somehow ended up dating. It was a slow progression that somehow happened in the blink of an eye.

I met J while also developing a poly relationship with a man. As our relationship progressed I took note of the differences and similarities in the dynamics.


In my opinion dates with men are always carefully curated, planned out and a timeline is set.

My dates with J were always more fluid, and we spent time together just getting to know each other and building a connection.

It certainly is easier dating a woman, they actually want to go shopping with you! I jest, but I felt like we were able to create a connection much easier than in my heterosexual relationships of the past.

I think certainly part of this is based on personality too. J had a calming presence to her and that benefited our interactions. But I would say bits of it is gender-based, when it comes to the fact that in my experience dates with men end in sex, or a vehicle to get to having sex. It felt more fluid with J and based around an emotional intimacy.

Discussing relationship boundaries.

When dating men it feels like pulling teeth to go through questions like, are we exclusive, what are we exactly. Making it step to step through relationship milestones can be incredibly tense.

But in my relationship with J, I was amazed at how easily we moved through relationship milestones. Saying the L word felt natural and easy. We talked about our boundaries and discussions when we upset each other for some reason, without it feeling like the world was ending.

We argued about small stuff, but we also made up easily, not something I was used to in my past straight relationships. But it seemed we also fell into a committed relationship quicker than I was used to.


Sex with a man or a woman is a completely different thing to each other, of course.

There is data that says lesbians have more orgasms than straight women, and its certainly correct data. Sex with women is fluid, intimate, and mutual pleasure focused.

But certainly, they each have their own wonderful points, sex with a man is amazing as well, in different ways.

Certainly in my view, its scary to have sex with a woman for the first time! The stereotype that women know each others bodies and thus the sex should be fantastic, can be valid. But what one women likes, isn’t the same as what someone else likes.

But hey, practice makes perfect?

Attention from the public.

It may be 2018 but homophobia is still alive and well. Two women together in public kissing and holding hands still gets attention and stares from the public.

Being someone used to public displays of affection with men in the past I never considered what others thought about it, I just did it.

But when dating J and undergoing PDA’s I was a little more cautious, it took awhile for me to not feel awkward in public. Soon, kissing her in public gave me a thrill.

Navigating Labels

Bisexuality is still seen as a ‘myth.’ It can be hard for people to understand that being bisexual does not mean you are straight but want to experiment, or that you are gay but afraid to fully admit it.

Just like being polyamorous, it is possible to love more than one person at a time, and be attracted to two or more different genders.

When you start dating a woman for the first time, I found people wanted to put labels on me. My being bi doesn’t change just because I am dating a man or a woman.

Don’t let people decide how you identify.

Women Are Amazing

Dating J has just made me realise how much I adore women. How smart, kind, and caring they are.

How much I miss touching women when I’m not dating one, their soft skin and bodies, their gentle touches and kisses. It’s something magical.

What I take away from my relationship with J is that dating women is not as scary as I thought it was. Instead it’s something magical that has taught me so much about myself, my sexuality, and women.

Rain Tiligadis is a young queer and poly Journalism student residing in Melbourne. She can be found writing for a range of publications, including SBSJUNKEE, and more.